CN105419332A - Antibacterial composite material, preparation method and application thereof - Google Patents
Antibacterial composite material, preparation method and application thereof Download PDFInfo
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- CN105419332A CN105419332A CN201510979086.1A CN201510979086A CN105419332A CN 105419332 A CN105419332 A CN 105419332A CN 201510979086 A CN201510979086 A CN 201510979086A CN 105419332 A CN105419332 A CN 105419332A
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
The invention discloses an antibacterial composite material, which is composed of an antibacterial amphiphilic biological carbon material and resin. The antibacterial amphiphilic biological carbon material is prepared by modifying the surface of an amphiphilic biological carbon material with quaternized polyethyleneimine through a covalent bond with the amphiphilic biological carbon material as a carrier. Hydrophobic resin is uniformly doped with the antibacterial amphiphilic biological carbon material to form the antibacterial composite material. A preparation method is simple in process and easy to carry out. The novel antibacterial material is ecological and environment-friendly, is toxic-free and is not liable to permeate through skin. A finish product is durable and stable in antibacterial effect. When being used for producing medical apparatus and instruments, such as catheters and the like, the antibacterial composite material can significantly reduce the infection rate of urinary system, thereby reducing patient suffering and reducing treatment cost. The invention also discloses the preparation method of the composite material.
Description
Technical field
The present invention relates to a kind of antimicrobial form matrix material, particularly a kind of antimicrobial form catheter.
Background technology
Surperficial non-specific adsorption/the adhesion of protein/bacterium is the major reason that implements surface forms biofouling.Usually, first protein will at material surface formation condition layer, and then cause the sticking of bacterium, breed and finally form microbial film by non-specific adsorption.In this research field, people mainly adopt the strategy reply protein of surface grafting hydrophilic polymer and the double challenge of bacterium at present, and these hydrophilic polymers comprise polyoxyethylene glycol/polyoxyethylene, poly-hydroxyethyl methacrylate and poly-N-(2-hydroxypropyl) methacryloyl, carboxylic acid beet alkali ampholytic ionic copolymer etc.Although these hydrophilic polymer surfaces can by the strong hydrogen bond between hydrophilic polymer and water or ionization, induced surface formed hydration shell with stop/repel protein to approach with bacterium adherent, but, the antifouling property height of hydrophilic polymer relies on surface hydration, highly rely on physicochemical property (character of material surface, the roughness on surface, hydrophilic polymer is at the grafting density of material surface and thickness etc.), cause its surface modification process complicated and lengthy and tedious.Secondly, any extraneous factor affecting surface hydration all can affect the antifouling property of hydrophilic polymer.Such as, polyoxyethylene glycol exists at transition metal ion or can oxidative degradation gradually under aerobic conditions.In addition, for biomaterials such as catheter, implantable medical apparatus, people not only wish that its surface has low dirt or non-dirty characteristic, also wish that its surface has the effect protein of the degraded surface adsorption (or kill the bacterium of adhesion) of elimination protein/bacterium dirt.
Therefore, how to pass through simple and effective approach removes protein/bacterium dirt, reduce surface biological pollution, remain study hotspot and the difficult point in the fields such as current bio-chemistry separation, packaging material for food.Exploring wide spectrum, efficiently anti-biotic material is still the hot issue of scientists study.
Catheter is one of the most frequently used medicine equipment of hospital, and the urinary tract infections caused by catheter to be also modal a kind of clinical bacteria infect.It is the normal defense mechanisms that catheter can suppress or weaken body that self retaining catheter causes the topmost reason of urinary tract infections, causes the formation of bacterium compound film.This infection not only brings great misery to patient, but also consumes extra health resources.
For catheter, people not only wish that its surface has low dirt or non-dirty characteristic, also wish that its surface has the effect protein of the degraded surface adsorption (or kill the bacterium of adhesion) of elimination protein/bacterium dirt.
Therefore, how to pass through simple and effective approach removes protein/bacterium dirt, reduce surface biological pollution, remain study hotspot and the difficult point of current bio-medical material.
At present, the antibiotic catheters of state food pharmaceuticals administration general bureau approval only has three, Futaiminde Medicine Tech Co., Ltd., Beijing, Guangzhou Well Lead Medical Instruments Co., Ltd. and Mei Xin sunrise medicine equipment (Shanghai) Co., Ltd. respectively, its antibacterial effect all from be applied to catheter outside surface containing silver coating, once silver ions release is complete, catheter just loses anti-microbial effect.The antibacterial effect time is short, and for the patient needing Preserving time catheter, be easy to the infection causing urinary system, bring more misery to patient, ordinary urethral catheter does not have germicidal action, more easily causes the infection of urinary system.
In addition, nano-Ag particles, in the course of processing and catheter preparation process, as pressed powder or other forms, can enter human body by approach such as respiratory tract, digestive tube, skin and direct embeddings, produce potential harm to human body; Silver ions also can cause heavy metal contamination to environment, brings considerable damage to water body.
Summary of the invention
The object of this invention is to provide a kind of novel antibacterial type matrix material, can lasting stability ground effectively bacteria growing inhibiting, prepare with it infection problems that medicine equipment can avoid human organ.
Technical scheme of the present invention is as follows:
A kind of antimicrobial form matrix material, it is the antimicrobial form matrix material of a kind of germ resistance amphiphilic biological carbon material and resin composition, described germ resistance amphiphilic biological carbon material is for carrier with amphiphilic biological carbon material, the germ resistance amphiphilic biological carbon material of Quaternary Polyethyleneimine is modified with covalent linkage at amphiphilic biological carbon material surface, described germ resistance amphiphilic biological carbon homogenize material is doped in hydrophobic resin and forms antimicrobial form matrix material, described hydrophobic resin can be silicon rubber (dimethyl silicone rubber, methylethyl silicon rubber, methyl phenyl vinyl silicone rubber, fluorine-based silicon rubber) comprise medical grade silicon rubber, latex comprises medical latex, natural rubber comprises medical natural rubber and plastic cement comprises medical-grade plastics (as PVC polyvinyl chloride, PU urethane, PP polypropylene, PE polyethylene), preferably medical grade silicon rubber.
Above-mentioned antimicrobial form matrix material, described germ resistance amphiphilic biological carbon material and the mass ratio of resin are 1:100 ~ 1:50
Prepare a method for above-mentioned antimicrobial form matrix material, it comprises the steps:
The synthesis of step 1, polyethyleneimine: amination amphiphilic biological carbon particles of material:
Take amphiphilic biological carbon particles of material and be placed in centrifuge tube ultrasonic disperse in PB damping fluid (pH5.5), add successively in right amount excessive 1 ?(3 ?dimethylamino-propyl) ?3 ?ethyl-carbodiimide hydrochloride, N ?hydroxysuccinimide, be placed on afterwards (180r/min) shake well on shaking table 2 ?4h (carboxyl on activation amphiphilic biological carbon material), react rear PB buffer by centrifugation (10000r/min, 3min) wash 3 ?5 times, again gained solid is scattered in PB damping fluid again, then taking polymine (PEI) joins in described damping fluid, to be placed on shaking table (180r/min) shake well 8 ?10h, reacted rear distilled water centrifuge washing 3 ?5 times, put into 40 ° of vacuum drying ovens dry, obtain polyethyleneimine: amination amphiphilic biological carbon particles of material (ACPs ?PEI),
The preparation of step 2, Quaternary Polyethyleneimine amphiphilic biological carbon particles of material:
Take polyethyleneimine: amination amphiphilic biological carbon particles of material, ultrasonic disperse, in the three-necked bottle that DMF solvent is housed, adds hexyl bromide 1 bromohexane (CH
3(CH
2)
5br), the ratio of its addition and ACPs-PEI is 10:1ml/g, after mixed system ultrasonic disperse, add magneton stirring reaction 10-12h under constant temperature blender with magnetic force 90 DEG C of conditions, then temperature of reaction system is down to 50 DEG C and adds the methyl iodide (CH with hexyl bromide 1 bromohexane equivalent again
3i), continue stirring reaction 10-12h, reaction terminates to carry out suction filtration to reaction solution afterwards, and thoroughly washs particulate with ethanol and distilled water respectively, put into 40 DEG C of vacuum drying ovens dry, obtain Quaternary Polyethyleneimine amphiphilic biological carbon particles of material (ACPs-QPEI);
The preparation of step 3, above-mentioned antimicrobial form matrix material:
By Quaternary Polyethyleneimine amphiphilic biological carbon particles of material and resin blended or mixing with mass ratio 1:100 ~ 1:50, obtain antimicrobial form matrix material.
Above-mentioned preparation method, the mass ratio of the amphiphilic biological carbon particles of material described in step 1 and 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride, N-hydroxysuccinimide, polymine is 1:1 ~ 4:1 ~ 4:1 ~ 3.
Above-mentioned preparation method, the ratio of the amphiphilic biological carbon particles of material that described described in step 2 crosses with polyethylene imine beautify and 1-bromo hexane, methyl iodide is 1g:5 ~ 15ml:5 ~ 15ml.
Above-mentioned preparation method, blended described in step 3 is when described resin is silicon rubber, can prepare as follows: take a certain amount of silicon rubber, take Quaternary Polyethyleneimine carbon material particulate again, add in a small amount of acetone, ultrasonicly make after Quaternary Polyethyleneimine carbon material particulate scatter completely, pour the acetone soln containing Quaternary Polyethyleneimine carbon material particulate in silicon rubber ultrasonic agitation, add silicon rubber solidifying agent subsequently, put into vacuum drying oven vacuum after abundant stirring and pump silicon rubber bubble, namely the antimicrobial form composite finished product of Quaternary Polyethyleneimine carbon material particulate/silicon rubber composition is obtained after solidification.
Above-mentioned preparation method, blended described in step 3 is when described resin is latex, can prepare as follows: take a certain amount of latex, take Quaternary Polyethyleneimine carbon material particulate again, Quaternary Polyethyleneimine carbon material particulate is added to carry out in the latex after plasticating mixing, mixing evenly after, sulfuration obtains the antimicrobial form composite finished product of Quaternary Polyethyleneimine carbon material particulate/latex composition.
Above-mentioned preparation method, blended described in step 3 is when described resin is plastic cement, can prepare as follows: take a certain amount of plastic cement, take Quaternary Polyethyleneimine carbon material particulate again, Quaternary Polyethyleneimine carbon material particulate is added to carry out in plastic cement mixing, mixing evenly after, pelletizing, the pellet of the antimicrobial form matrix material of obtained Quaternary Polyethyleneimine carbon material particulate/plastic cement composition.
Above-mentioned antimicrobial form matrix material can conveniently technique be prepared medicine equipment, toy for children and need to prevent the utensil of bacteriological infection.
Above-mentioned antimicrobial form matrix material is being prepared medicine equipment, toy for children and is being needed the application that prevents in the utensil of bacteriological infection.
The application in catheter prepared by the antimicrobial form matrix material of the Quaternary Polyethyleneimine carbon material particulate of above-mentioned antimicrobial form matrix material and medical grade silicon rubber composition.
Beneficial effect of the present invention: the invention provides a kind of novel antibacterial catheter and preparation method thereof, its antibacterial effect is from this novel antibacterial material Quaternary Polyethyleneimine amphiphilic biological carbon particles of material, this novel antibacterial material ecological, environmental protective, can not cause secondary pollution to environment.Joined in the starting material of catheter, its antibacterial effect significantly (see Fig. 9, Figure 10), does not affect the raw-material tensile property of catheter and physiological inertia, has no stimulation to skin.Because feed postition is that this novel antibacterial homogenize material is mixed in catheter body, is contact sterilization, not only can kills the bacterium outside human body, also intravesical bacterium can be killed and remove, effectively prevent the infection problems of urinary system with lasting stability.Meanwhile, the indwelling time of catheter can also be extended, decrease the pain of injury because displacement catheter brings to patient, reduce medical expense.Preparation method's technique of the present invention is simple, easy to operate.
Accompanying drawing explanation
Fig. 1, the dispersiveness figure of Quaternary Polyethyleneimine amphiphilic biological carbon particles of material in different solvents.Wherein a is water, and b is acetone, and c is chloroform, and d is toluene, and e is DMF, and f is water and chloroform mixed system.
The grain size distribution of Fig. 2, Quaternary Polyethyleneimine amphiphilic biological carbon particles of material.PDI represents size distribution index.
The potential ph diagram ph of Fig. 3, Quaternary Polyethyleneimine amphiphilic biological carbon particles of material.
Fig. 4, Quaternary Polyethyleneimine amphiphilic biological carbon particles of material are to the antibacterial effect figure of streptococcus aureus.
Fig. 5, Quaternary Polyethyleneimine amphiphilic biological carbon particles of material are to colibacillary antibacterial effect figure.
Fig. 6, Quaternary Polyethyleneimine amphiphilic biological carbon particles of material dispersed picture in silicon rubber.
Fig. 7, add the silicon rubber picture of amphipathic biological amphiphilic biological carbon particles of material and Quaternary Polyethyleneimine amphiphilic biological carbon particles of material.
Fig. 8, prepare silica fubber cathete material object.Blank silica fubber cathete (left side), add ACPs silica fubber cathete (in), add the silica fubber cathete (right side) of ACPs-QPEI.
The contact angle figure of Fig. 9, different film.Wherein, a=107.5 °, is silicone rubber membrane (SR); B=88.5 °, for adding the silicone rubber membrane (SR/ACPs) of amphipathic biological carbon particles of material; C=85 °, for adding the silicone rubber membrane (SR/ACPs-QPEI) of Quaternary Polyethyleneimine amphiphilic biological carbon particles of material.
Figure 10, different film are to streptococcus aureus anti-bacterial attachment picture.A is silicone rubber membrane (SR), b is the silicone rubber membrane (SR/ACPs) adding amphipathic biological carbon particles of material, C is the silicone rubber membrane (SR/ACPs-PEI) adding polyethyleneimine: amination amphiphilic biological carbon particles of material, and d is the silicone rubber membrane (SR/ACPs-QPEI) adding Quaternary Polyethyleneimine carbon slag particulate.
Antibacterial effect--the reusing design sketch of the silicone rubber membrane of Figure 11, interpolation Quaternary Polyethyleneimine amphiphilic biological carbon particles of material.
Embodiment
Below in conjunction with specific embodiment, the present invention is described in detail:
Embodiment 1 prepares Quaternary Polyethyleneimine amphiphilic biological carbon particles of material
(1) 10g yeast is jolted dispersion, get its upper strata canescence bacteria suspension centrifugal, discard waste liquid, then 20ml acetone is added, jolt 5-20min, centrifugal, discard acetone, with method repetitive operation 3-5 time, by substrate with 2% glutaraldehyde water solution dispersion, pour in high-temperature high-pressure reaction kettle, at 150-200 DEG C, react 8-10h, after reaction terminates, be chilled to room temperature, outwell upper solution, by lower sediment distilled water supersound washing repeatedly, be finally placed in baking oven and be drying to obtain amphipathic biological carbon particles of material.
(2) amphipathic biological carbon particles of material 200mg ultrasonic disperse is taken in 20mlPB damping fluid (PH5.5), add excessive in right amount 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride, N-hydroxysuccinimide successively, shake well 2h afterwards, react rear PB buffer by centrifugation (10000r/min, 3min) and wash 3 times.Be scattered in 20mlPB damping fluid by gained precipitation again, then add 200mg polymine (PEI), shake well reaction 8h, has reacted rear distilled water centrifuge washing 3 times, in 40 ° of lower forced air dryings.Products therefrom is polyethyleneimine: amination amphiphilic biological carbon particles of material (being abbreviated as ACPs-PEI).
(3) the polyethyleneimine: amination carbon slag microparticulate ultrasound taking 200mg is scattered in DMF, then adds a certain amount of hexyl bromide 1 bromohexane (CH
3(CH
2)
5br), the ratio of its addition and ACPs-PEI is 10:1ml/g, and after mixed system ultrasonic disperse, stirring reaction 12h under 90 DEG C of conditions, is then down to 50 DEG C and adds the methyl iodide (CH with hexyl bromide 1 bromohexane equivalent again by temperature of reaction system
3i), stirring reaction 12h is continued.Reaction terminates to carry out suction filtration to reaction solution afterwards, and thoroughly washs particulate with ethanol and distilled water respectively, in 40 ° of lower forced air dryings.Products therefrom is Quaternary Polyethyleneimine amphiphilic biological carbon particles of material (being abbreviated as ACPs-QPEI).
Embodiment 2 prepares Quaternary Polyethyleneimine carbon slag particulate/silastic mixture
Quaternary Polyethyleneimine carbon slag particulate 50mg is joined in 5g silastic liquid according to the ratio that massfraction is 1:100, fully mixes;
1, antimicrobial silicon rubber urinary catheter is prepared
The preparation technology of said mixture conveniently catheter is made novel antibacterial catheter.
2, tensile property, tear resistance, Young's modulus and elongation at break and Shore A hardness test result
3, antibacterial effect test result
Select intestinal bacteria (E.coli) strain isolated as the Gram-negative bacteria of the anti-microbial activity of test membrane and select streptococcus aureus (S.aureus) strain isolated as the gram-positive microorganism of the anti-microbial activity of test membrane, antibacterial granule test result is as Fig. 4, Fig. 5, as seen from the figure, the minimum inhibitory concentration (MIC) of Quaternary Polyethyleneimine carbon slag particulate to Gram-negative bacteria intestinal bacteria (E.coli) is about 3.0mg/ml, be about 1.0mg/ml to the minimum inhibitory concentration (MIC) of gram-positive microorganism streptococcus aureus (S.aureus), antibacterial granule/silicon rubber composite material the antibacterium being added to 1wt% sticks result as Fig. 9, Figure 10.
The foregoing is only preferred embodiment of the present invention; not in order to limit the present invention; when not deviating from the present invention's spirit and essence thereof, any amendment done, equivalent to replace and improvement etc., within the protection domain that all should be included in the claim appended by the present invention.
Claims (11)
1. an antimicrobial form matrix material, it is characterized in that: it is the antimicrobial form matrix material of a kind of germ resistance amphiphilic biological carbon material and resin composition, described germ resistance amphiphilic biological carbon material is for carrier with amphiphilic biological carbon material, the germ resistance amphiphilic biological carbon material of Quaternary Polyethyleneimine is modified with covalent linkage at amphiphilic biological carbon material surface, described germ resistance amphiphilic biological carbon homogenize material is doped in hydrophobic resin and forms antimicrobial form matrix material, described hydrophobic resin is silicon rubber, comprise medical grade silicon rubber, latex, comprise medical latex, plastic cement, comprise medical-grade plastics.
2. antimicrobial form matrix material according to claim 1, is characterized in that: described hydrophobic resin is medical latex, medical grade silicon rubber, medical-grade plastics.
3. antimicrobial form matrix material according to claim 1, is characterized in that: described germ resistance amphiphilic biological carbon material and the mass ratio of resin are 1:100 ~ 1:50.
4. prepare a method for antimicrobial form matrix material described in claim 1, it is characterized in that it comprises the steps:
The synthesis of step 1, polyethyleneimine: amination amphiphilic biological carbon particles of material:
Take amphiphilic biological carbon particles of material and be placed in centrifuge tube ultrasonic disperse in PB damping fluid (pH5.5), add successively in right amount excessive 1 ?(3 ?dimethylamino-propyl) ?3 ?ethyl-carbodiimide hydrochloride, N ?hydroxysuccinimide, be placed on afterwards (180r/min) shake well on shaking table 2 ?4h (carboxyl on activation amphiphilic biological carbon material), react rear PB buffer by centrifugation (10000r/min, 3min) wash 3 ?5 times, again gained solid is scattered in PB damping fluid again, then taking polymine (PEI) joins in described damping fluid, to be placed on shaking table (180r/min) shake well 8 ?10h, reacted rear distilled water centrifuge washing 3 ?5 times, put into 40 DEG C of vacuum drying ovens dry, obtain polyethyleneimine: amination amphiphilic biological carbon particles of material (ACPs ?PEI),
The preparation of step 2, Quaternary Polyethyleneimine amphiphilic biological carbon particles of material:
Take polyethyleneimine: amination amphiphilic biological carbon particles of material, ultrasonic disperse, in the three-necked bottle that DMF solvent is housed, adds hexyl bromide 1 bromohexane (CH
3(CH
2)
5br), the ratio of its addition and ACPs-PEI is 10:1ml/g, after mixed system ultrasonic disperse, add magneton stirring reaction 10-12h under constant temperature blender with magnetic force 90 DEG C of conditions, then temperature of reaction system is down to 50 DEG C and adds the methyl iodide (CH with hexyl bromide 1 bromohexane equivalent again
3i), continue stirring reaction 10-12h, reaction terminates to carry out suction filtration to reaction solution afterwards, and thoroughly washs particulate with ethanol and distilled water respectively, put into 40 DEG C of vacuum drying ovens dry, obtain Quaternary Polyethyleneimine amphiphilic biological carbon particles of material (ACPs-QPEI);
The preparation of step 3, above-mentioned antimicrobial form matrix material:
By Quaternary Polyethyleneimine amphiphilic biological carbon particles of material and resin blended or mixing with mass ratio 1:100 ~ 1:50, obtain antimicrobial form matrix material.
5. preparation method according to claim 4, is characterized in that: the mass ratio of the amphiphilic biological carbon particles of material described in step 1 and 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride, N-hydroxysuccinimide, polymine is 1:1 ~ 4:1 ~ 4:1 ~ 3.
6. preparation method according to claim 4, is characterized in that: the ratio of the amphiphilic biological carbon particles of material crossed with polyethylene imine beautify described in step 2 and 1-bromo hexane, methyl iodide is 1g:5 ~ 15ml:5 ~ 15ml.
7. preparation method according to claim 4, it is characterized in that: blended described in step 3 is when described resin is silicon rubber, can prepare as follows: take a certain amount of silicon rubber, take Quaternary Polyethyleneimine carbon material particulate again, add in a small amount of acetone, ultrasonicly make after Quaternary Polyethyleneimine carbon material particulate scatter completely, pour the acetone soln containing Quaternary Polyethyleneimine carbon material particulate in silicon rubber ultrasonic agitation, add silicon rubber solidifying agent subsequently, put into vacuum drying oven vacuum after abundant stirring and pump silicon rubber bubble, namely the antimicrobial form composite finished product of Quaternary Polyethyleneimine carbon material particulate/silicon rubber composition is obtained after solidification.
8. preparation method according to claim 4, it is characterized in that: blended described in step 3 is when described resin is latex, can prepare as follows: take a certain amount of latex, take Quaternary Polyethyleneimine carbon material particulate again, Quaternary Polyethyleneimine carbon material particulate is added to carry out in the latex after plasticating mixing, mixing evenly after, sulfuration obtains the antimicrobial form composite finished product of Quaternary Polyethyleneimine carbon material particulate/latex composition.
9. preparation method according to claim 4, it is characterized in that: blended described in step 3 is when described resin is plastic cement, can prepare as follows: take a certain amount of plastic cement, take Quaternary Polyethyleneimine carbon material particulate again, Quaternary Polyethyleneimine carbon material particulate is added to carry out in plastic cement mixing, mixing evenly after, pelletizing, the pellet of the antimicrobial form matrix material of obtained Quaternary Polyethyleneimine carbon material particulate/plastic cement composition.
10. antimicrobial form matrix material according to claim 1 is being prepared medicine equipment, toy for children and is being needed the application that prevents in the utensil of bacteriological infection.
The application in catheter prepared by the antimicrobial form matrix material of the Quaternary Polyethyleneimine carbon material particulate of 11. antimicrobial form matrix materials according to claim 1 and medical grade silicon rubber composition.
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| CN105641735A (en) * | 2016-04-07 | 2016-06-08 | 北京化工大学 | Preparation method of antibacterial polysaccharide hemostatic cotton based gauze |
| CN106675146A (en) * | 2016-12-05 | 2017-05-17 | 周恩洪 | Antibacterial leather and method of preparing antibacterial leather |
| CN107638873A (en) * | 2017-08-23 | 2018-01-30 | 南昌大学 | A kind of preparation method of the nitrogen co-doped biomass-based porous carbon material of phosphorus for Cr VI absorption |
| CN109122678A (en) * | 2018-07-13 | 2019-01-04 | 郑州欧姆康生物材料有限公司 | A kind of nano-silver loaded is in the nano-ag composite and its preparation method and purposes of amphipathic biological carbon material |
| CN109568679A (en) * | 2018-11-18 | 2019-04-05 | 西南交通大学 | A kind of biodegradable polyurethane sheath and preparation method thereof with antibacterial functions |
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| CN110469072A (en) * | 2019-08-20 | 2019-11-19 | 湖北亮达铝业科技有限公司 | A kind of organic anti-bacterial coating aluminum section |
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| CN112724549A (en) * | 2020-12-03 | 2021-04-30 | 广东祺龙科技有限公司 | Heat-insulating mildew-proof antibacterial curtain material and preparation method and application thereof |
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| CN105641735A (en) * | 2016-04-07 | 2016-06-08 | 北京化工大学 | Preparation method of antibacterial polysaccharide hemostatic cotton based gauze |
| CN105641735B (en) * | 2016-04-07 | 2018-09-21 | 北京化工大学 | A kind of preparation method of antibiotic property polysaccharide hemostatic cotton base gauze |
| CN106675146A (en) * | 2016-12-05 | 2017-05-17 | 周恩洪 | Antibacterial leather and method of preparing antibacterial leather |
| CN107638873A (en) * | 2017-08-23 | 2018-01-30 | 南昌大学 | A kind of preparation method of the nitrogen co-doped biomass-based porous carbon material of phosphorus for Cr VI absorption |
| CN109122678A (en) * | 2018-07-13 | 2019-01-04 | 郑州欧姆康生物材料有限公司 | A kind of nano-silver loaded is in the nano-ag composite and its preparation method and purposes of amphipathic biological carbon material |
| CN109568679A (en) * | 2018-11-18 | 2019-04-05 | 西南交通大学 | A kind of biodegradable polyurethane sheath and preparation method thereof with antibacterial functions |
| CN110448735A (en) * | 2019-07-04 | 2019-11-15 | 郑州欧姆康生物材料有限公司 | A kind of amphiphilic biology carbon complex and its preparation method and purposes with antibiosis anticoagulative |
| CN110469072A (en) * | 2019-08-20 | 2019-11-19 | 湖北亮达铝业科技有限公司 | A kind of organic anti-bacterial coating aluminum section |
| CN111763329A (en) * | 2020-05-25 | 2020-10-13 | 上海麟定生物科技有限公司 | Quaternized polyethyleneimine modified graphene quantum dot, and preparation method and application thereof |
| CN112724549A (en) * | 2020-12-03 | 2021-04-30 | 广东祺龙科技有限公司 | Heat-insulating mildew-proof antibacterial curtain material and preparation method and application thereof |
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